JPH093350A - Blue disperse dye mixture - Google Patents

Abstract

PURPOSE: To obtain a blue disperse dye mixture excellent in temp. dependence and improved in light fastness and dyeing properties by mixing two specific monoazo dyes. CONSTITUTION: This dye mixture is obtd. by mixing 1 pt.wt. monoazo dye represented by the formula I (X is a halogen; R<1> is a 1-5C alkyl; R<2> is a 1-4C alkyl; and R<3> is a 1-5C alkyl or aryl) with 0.05-1.0 pt.wt. monoazo dye represented by the formula II (R<4> is a 1-5C alkyl; R<5> is a 2-3C alkylene; R<6> is a 1-4C alkyl; and R<7> is H or a 1-5C alkyl).

Description

Detailed Description of the Invention

[0001]

This invention relates to disperse dye mixtures. More specifically, the present invention relates to a blue disperse dye mixture having excellent temperature dependency, light fastness and dyeing property (build-up property) during dyeing.

[0002]

2. Description of the Related Art Monoazo dyes represented by the following general formula [1] have excellent light fastness, but have insufficient temperature dependence. On the other hand, the dyeing property (build-up property) also needs to be improved, especially in the field of medium density dyeing.

[0003]

Embedded image

(In the formula, X represents a halogen atom, and R ¹
Represents C ₁ -C ₅ alkyl group, R ² represents a C ₁ -C ₄ alkyl group, R ³ represents a C ₁ -C ₅ alkyl group or an allyl group. )

On the other hand, the monoazo dye represented by the following general formula [2] is excellent in temperature dependence, but inferior in light fastness to [1], and in addition, it has a dyeing property (building) in the field of medium density dyeing. Up) is not sufficient and needs to be improved.

[0006]

Embedded image

(In the formula, X represents a halogen atom, and R ⁴
Represents C ₁ -C ₅ alkyl group, R ⁵ represents a C ₂ -C ₃ alkylene group, R ⁶ represents a C ₁ -C ₄ alkyl radical, R ⁷ is a hydrogen atom or a C ₁ -C ₅ alkyl group Represents )

[0008]

DISCLOSURE OF THE INVENTION The present inventors have aimed to develop a blue disperse dye having excellent temperature dependence, light fastness and dyeing property (build-up property). The present invention has been achieved by paying attention to the dyes represented by 1] and [2] and repeating research.

[0009]

In the present invention, 0.05 to 1.0 of the monoazo dye represented by the following general formula [2] is added to 1 part by weight of the monoazo dye represented by the following general formula [1].
The gist of the invention is a blue disperse dye mixture prepared by blending parts by weight and a dyeing method using the same.

[0010]

Embedded image

(In the formula, X represents a halogen atom, and R ¹
Represents C ₁ -C ₅ alkyl group, R ² represents a C ₁ -C ₄ alkyl group, R ³ represents a C ₁ -C ₅ alkyl group or an allyl group. )

[0012]

[Chemical 6]

(In the formula, X represents a halogen atom, and R ⁴
Represents C ₁ -C ₅ alkyl group, R ⁵ represents a C ₂ -C ₃ alkylene group, R ⁶ represents a C ₁ -C ₄ alkyl radical, R ⁷ is a hydrogen atom or a C ₁ -C ₅ alkyl group Represents )

The present invention will be described in detail below. In the general formulas [1] and [2], R ¹ , R ³ , R ⁴ and R
^The C ₁ -C ₅ alkyl group represented by ⁷ may be linear or branched, R ¹ and R ⁴ are preferably methyl groups or ethyl groups, and R ³ and R ⁷ are C ₂ -C ₄ (linear Form) alkyl group, particularly ethyl group is preferable, and methyl group or ethyl group is preferable among the C ₁ -C ₄ alkyl groups represented by R ² and R ⁶ . The halogen atom represented by X is preferably a chlorine atom or a bromine atom.

The mixing ratio of the dyes represented by the general formulas [1] and [2] is 1 part by weight of the monoazo dye represented by the general formula [1], and the monoazo dye represented by the general formula [2] is 0.
05 to 1.0 part by weight, preferably 0.1 to 0.7 part by weight, particularly preferably 0.3 to 0.5 part by weight.

Further, if necessary, other blue dyes, for example, dyes represented by the following formulas may be used in combination at a ratio of 10% by weight or less, and in order to obtain a desired color tone, a yellow dye or a red dye is added. It can also be used.

[0017]

[Chemical 7]

The dyes represented by the above general formulas [1] and [2] are synthesized according to a known method. The dye mixture of the present invention has good leveling and reproducibility of ordinary polyester fibers composed of polyethylene terephthalate, polybutylene terephthalate, and other polycondensates of terephthalic acid and 1,4-bis- (hydroxymethyl) cyclohexane. Stain with a nice blue color. The form of the material to be dyed is a yarn made of polyester fiber, a woven fabric or cotton, silk, wool, rayon,
Examples include mixed fiber products with fibers such as polyamide and polyurethane.

In order to dye polyester fibers with the dye mixture of the present invention, the dyes represented by the above-mentioned general formulas [1] and [2] are insoluble or sparingly soluble in water. It is possible to prepare a dyeing bath or printing paste dispersed in an aqueous medium using a condensate of naphthalene sulfonic acid and formaldehyde, a higher alcohol sulfate, a higher alkylbenzene sulfonate, etc. as an agent, and to carry out by dipping or printing. it can.

For example, in the case of dip dyeing, a polyester fiber or a mixture thereof can be dyed with excellent fastness by applying a usual dyeing method such as a high temperature dyeing method and a thermosol dyeing method. In that case, if a well-known acidic substance such as formic acid, acetic acid, phosphoric acid or ammonium sulfate is added to the dyeing bath, a better result can be obtained.

The dye mixture of the present invention exhibits particularly excellent dyeing properties and temperature dependence when applied to the dip dyeing method. The dyeing conditions in exhaust dyeing are not particularly limited, and for example, the dyeing temperature is about 120 to 140 ° C., and the dyeing time is 30 to
It takes about 60 minutes and the pH of the dyeing bath is about 4 to 8.5. Furthermore, various leveling agents and ultraviolet absorbers may be used in combination.

[0022]

EXAMPLES Next, the present invention will be described more specifically by way of examples, but the present invention is not limited to the following examples unless it exceeds the gist.

Example 1 A blue disperse dye mixture comprising 35 g of a dye represented by the following structural formula (1-1) and 15 g of a dye represented by the following structural formula (2-1).

[0024]

Embedded image

Lignin sulfonic acid formalin condensate 1
50 g and 650 g of water were mixed, wet-milled with a sand grinder, and spray-dried. To each of 0.05 g and 0.25 g of this powdery dye mixture, 0.08 g of nonionic leveling agent Diaserver (registered trademark) LR-PSL (manufactured by Mitsubishi Chemical Co., Ltd.) and 150 ml of water were added to prepare a dyeing bath. Adjust the pH to 4.5 with acetic acid / sodium acetate system or potassium dihydrogen phosphate / disodium hydrogen phosphate system, add 5 g of polyester fabric, and 130 ° C and 1
Exhaust dyeing was carried out at 20 ° C. for 60 minutes, then soaping, washing with water and drying to obtain a relatively vivid blue dyeing.

The resulting dyed fabric was evaluated for temperature dependency, build-up property and light fastness according to the following methods.
The results are shown in Table 1. Temperature dependence: 13 at pH 4.5 with 0.25 g of dye
The density of the dyed cloth when dyed at 0 ° C. for 60 minutes was set to 100, and the density of the dyed cloth when dyed at 120 ° C. for 60 minutes without changing the amount of dye and the pH was shown as a relative value. In addition, the density measurement is performed by a color difference meter
The K / S value was obtained from the reflectance of the dyed product obtained by using a colorimeter, MS-2020).

Build-up property: Under the same conditions, except that 0.05 g of dye was used and the concentration of the dyed cloth when dyed at 130 ° C. for 60 minutes at pH 4.5 was 100 and the amount of dye was 0.25 g. The density of the dyed cloth when dyed is shown as a relative value. Light fastness: 13 at pH 4.5 with 0.05 g of dye
JIS L08 for dyeing cloth when dyed at 0 ° C for 60 minutes
According to No. 42, the carbon arc light was irradiated for 20 hours, and the degree of fading was judged on a blue scale.

Comparative Example 1 In Example 1, the dye represented by (2-1) was not used, and the amount of the dye represented by (1-1) used was from 35 g to 5 g.
Dyeing was performed according to Example 1 except that the amount was changed to 0 g. The results are shown in Table 1.

Comparative Example 2 According to Example 1, except that the dye represented by (1-1) was not used and the amount of the dye represented by (2-1) used was changed from 15 g to 50 g. And dyed. The results are shown in Table 1.

Examples 2 to 3 Dyeing was carried out according to the method of Example 1 except that the compounding amounts of the dyes (1-1) and (2-1) in Example 1 were changed as shown in Table 1. I did. The results are shown in Table 1.

[0031]

[Table 1]

Examples 4 to 20 35 parts by weight of the dye shown in Table 2 as the dye represented by the general formula [1] and the dye or dye listed in Table 2 as the dye represented by the general formula [2] Dyeing was carried out according to Example 1 using a dye mixture consisting of 15 parts by weight of the mixture. In any of the examples, the evaluation results of the obtained dyed fabrics were excellent as follows.

Temperature dependency: 92 or more Build-up property: 430 or more Light fastness: Grade 5 or more

[0034]

[Table 2]

[0035]

[Table 3]

[0036]

[Table 4]

[0037]

[Table 5]

[0038]

[Table 6]

[0039]

[Table 7]

[0040]

The blue disperse dye mixture of the present invention is excellent in temperature dependence, build-up property and light fastness.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Yosuke Takahashi 1-1 Kurosaki Shiroishi, Hachimansai-ku, Kitakyushu City Mitsubishi Kasei Hoechst Co., Ltd.

Claims (4)

[Claims] 1. A blue-based dispersion prepared by blending 0.05 to 1.0 part by weight of a monoazo dye represented by the following general formula [2] with 1 part by weight of the monoazo dye represented by the following general formula [1]. Dye mixture. Embedded image (In the formula, X represents a halogen atom, and R ¹ is C _{1 to} C ₅
It represents an alkyl group, R ² represents a C ₁ -C ₄ alkyl group, and R ³ represents a C ₁ -C ₅ alkyl group or an allyl group. ) (In the formula, X represents a halogen atom, and R ⁴ is C _{1 to} C ₅
Represents an alkyl group, R ⁵ represents a C _{2 to} C ₃ alkylene group, R ⁶ represents a C _{1 to} C ₄ alkyl group, and R ⁷ represents a hydrogen atom or a C _{1 to} C ₅ alkyl group. ) 2. In the general formula [1], X is a chlorine atom or a bromine atom, R ¹ and R ² are methyl groups or ethyl groups, and R ³ is a C ₂ -C ₄ alkyl group, Formula [2]
Wherein X is a chlorine atom or a bromine atom, R ⁴ and R ⁶ are methyl groups or ethyl groups, R ⁵ is a C ₂ -C ₃ alkylene group, and R ⁷ is a C ₂ -C ₄ alkyl group. The blue disperse dye mixture according to claim 1. 3. A monoazo dye 1 represented by the general formula [1].
The blue disperse dye mixture according to claim 1, wherein 0.1 to 0.7 parts by weight of the monoazo dye represented by the general formula [2] is blended with respect to parts by weight. 4. A dyeing method for polyester-containing fibers, which comprises using the blue disperse dye mixture according to any one of claims 1, 2 and 3.